PHENCYCLIDINE Latest Revision: May 16, 2005
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1 PHENCYCLIDINE Latest Revision: May 16, SYNONYMS CFR: Phencyclidine CAS #: Base: Hydrochloride: Other Names: 1-(1-Phenylcyclohexyl) piperidine PCP Angel dust CI-395 Sernylan Sernyl 2. CHEMICAL AND PHYSICAL DATA 2.1. CHEMICAL DATA Form Chemical Formula Molecular Weight Melting Point ( C) Base C 17 H 25 N Hydrochloride C 17 H 26 NCl SOLUBILITY Form A C E H M W Base FS FS FS FS S VSS Hydrochloride SS FS I I FS FS A = acetone, C = chloroform, E = ether, H = hexane, M = methanol and W = water, VS = very soluble, FS = freely soluble, S = soluble, PS = sparingly soluble, SS = slightly soluble, VSS = very slightly soluble and I = insoluble
2 3. SCREENING TECHNIQUES 3.1. COLOR TESTS REAGENT p-dimethylaminobenzaldehyde COLOR PRODUCED Red 3.2. CRYSTAL TESTS REAGENT Potassium permanganate CRYSTALS FORMED Bow-tie shaped 3.3. THIN-LAYER CHROMATOGRAPHY Visualization Acidified iodoplatinate spray Dragendorff spray COMPOUND RELATIVE R 1 System TLC17 System TLC11 System TLC16 piperidine PCP piperidinocyclohexylcarbonitrile (PCC) Both iodoplatinate and Dragendorff sprays will detect the three components. Iodine vapor produces a white spot outlined in brown for PCC, where as PCP and piperidine both give brown spots GAS CHROMATOGRAPHY Method PCP-GCS1 Instrument: Column: Gas chromatograph operated in split mode with FID 5% phenyl/95% methyl silicone 12 m x 0.2 mm x 0.33 µm film thickness
3 Carrier gas: Helium at 1.0 ml/min Temperatures: Injector: 270 C Detector: 280 C Oven program: 1) 175 C initial temperature for 1.0 min 2) Ramp to 275 C at 15 C/min 3) Hold final temperature for 3.0 min Injection Parameters: Split Ratio = 60:1, 1 µl injected Samples are to be dissolved or diluted in chloroform and filtered. COMPOUND RRT COMPOUND RRT nicotinamide 0.31 theophylline 1.15 benzocaine 0.49 chlorpheniramine 1.19 PCC 0.50 procaine 1.21 ibuprofen 0.53 methaqualone 1.44 acetaminophen 0.63 cocaine 1.52 phenacetin 0.65 tetracaine 1.55 pentobarbital 0.72 tetracosane 1.73 secobarbital 0.80 codeine 1.81 caffeine 0.88 morphine 1.89 diphenhydramine 0.95 acetylcodeine 2.00 antipyrine 0.97 O 6 -monoacetylmorphine 2.02 lidocaine 0.97 heroin 2.19 phencyclidine 1.00 (3.50 min) quinidine 2.45 aminopyrine 1.06 quinine 2.46 phenobarbital 1.11
4 3.5. HIGH PERFORMANCE LIQUID CHROMATOGRAPHY Method PCP-LCS1 Instrument: Column: Detector: Flow: High performance liquid chromatograph equipped with diode array 5 µm ODS, 150 mm x 4.6 mm UV, 210 nm 1.0 ml/min Injection Volume: 5.0 µl Buffer: Mobile Phase: 4000 ml distilled water, 10 g sodium hydroxide, 30.0 ml phosphoric acid and 8.0 ml hexylamine 1) Initially, buffer: acetonitrile 98:2 for 2 min 2) Gradient to buffer: acetonitrile 80:20 over 12 min 3) Gradient to buffer: acetonitrile 60:40 over 13 min 4) Hold buffer: acetonitrile 60:40 for 5 min Samples are to be dissolved in buffer: acetonitrile 90:10, sonicated, then filtered with a 0.45-micron filter. COMPOUND RRT COMPOUND RRT isonicotinamide 0.11 tropacocaine 0.71 nicotinamide 0.11 benzoylecgonine 0.72 morphine 0.19 antipyrine 0.76 phenylpropanolamine 0.19 cocaine 0.77 ephedrine 0.23 acetylcodeine 0.79 aminopyrine 0.25 heroin 0.83 procaine 0.27 phencyclidine 1.00 amphetamine 0.29 aspirin 1.08 methamphetamine 0.33 diazepam 1.13 codeine 0.35 t-cinnamoylcocaine 1.14 methylenedioxy-amphetamine 0.38 phenobarbital 1.19 methylenedioxy-methamphetamine 0.41 tetracaine 1.19
5 lidocaine 0.42 phenacetin 1.21 quinine 0.44 diphenhydramine 1.22 O 6 -monoacetylmorphine 0.49 phenyl-2-propanone 1.23 acetaminophen 0.51 benzocaine 1.29 strychnine 0.62 amobarbital 1.52 caffeine 0.65 methaqualone 1.56 barbital 0.67 secobarbital SEPARATION TECHNIQUES In general, phencyclidine can be extracted by dissolving the sample in dilute acid, making the solution basic, extracting with petroleum ether and recrystallizing as the hydrochloride salt form. Plant material that has been impregnated with phencyclidine in solution can be extracted using column chromatography. The plant material is incorporated directly into a 1 N HCl celite column. Elute phencyclidine from the column with water-washed chloroform. Evaporate the eluent to dryness. The resulting phencyclidine hydrochloride residue is then cleaned by washing with acetone, which will remove plant material related impurities. Contaminants from synthesis mixtures of phencyclidine in solution can be removed by an acid-base extraction procedure in which phencyclidine hydrochloride ion-pairs in chloroform. To a 125 ml separatory funnel add 2 ml of PCP sample, 50 ml of water, 50 ml of diethyl ether, and 5-7 drops of concentrated sodium hydroxide. Check ph to ensure aqueous phase is basic. Shake the funnel well, allow the layers to separate, and discard the aqueous layer leaving the ether (top layer) in the funnel. Wash the ether layer with 50 ml of water, shake, separate the layers and again discard the water, leaving the ether in the funnel. Add another 50 ml portion of water to the separatory funnel, and slowly add 5-7 drops of sulfuric acid to acidify the aqueous phase. Check the ph and add more acid if necessary to ensure that the aqueous phase is acidic. Shake the funnel, allow layers to separate and discard the ether portion. Return the aqueous layer to the separatory funnel and wash with a second portion of ether. Place the aqueous phase back into the separatory funnel and add one gram of sodium chloride to the acidic aqueous phase. Mix the solution until all the sodium chloride is dissolved. Add 50 ml of chloroform and extract. Save the chloroform (bottom layer) in a beaker. Perform a second chloroform extraction and combine with the first chloroform fraction. Evaporate the chloroform to dryness to recover the phencyclidine hydrochloride. 5. QUANTITATIVE PROCEDURES 5.1. GAS CHROMATOGRAPHY Method PCP-GCQ1 Internal Standard Stock Solution: 0.4 mg/ml docosane in chloroform.
6 Standard Solution Preparation: Accurately weigh and prepare a standard solution of phencyclidine (hydrochloride or base) at approximately 0.4 mg/ml using above internal standard stock solution. Sample Preparation: Powder: Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution. If necessary, dilute the sample so the final concentration approximates the standard concentration. Liquid: Accurately pipette an aliquot of the sample into a volumetric flask and dilute to volume with internal standard stock solution. Dilute the sample so the final concentration approximates the standard concentration. Plant material: Accurately weigh an amount of sample into a container and add an accurate volume of internal standard stock solution. Allow the phencyclidine to extract from the plant material for at least two hours. If necessary, dilute the sample so the final concentration approximates the standard concentration. Filter sample prior to injection. Instrument: Column: Carrier gas: Gas chromatograph operated in split mode with FID 5% phenyl/95% methyl silicone 12 m x 0.20 mm x 0.33µm film thickness Helium 1.0 ml/min Temperatures: Injector: 230 C Detector: 280 C Oven program: 1) 200 C initial temperature for 1.2 min 2) Ramp to 270 C at 30 C/min 3) Hold final temperature for 2.0 min Injection Parameters: Typical Retention Time: Linear Range: Split Ratio = 50:1, 1 µl injected Phencyclidine: 2.15 min Docosane: 2.95 min Base: mg/ml Hydrochloride: mg/ml Repeatability: Base: RSD less than 0.3% Hydrochloride: RSD less than 0.6% Correlation Coefficient: Base: Hydrochloride: Accuracy: Base: Error less than 5% Hydrochloride: Error less than 5%
7 The following compounds typically found in liquid phencyclidine samples were found to separate with a resolution greater than 1.5: piperidine cyclohexanone bromobenzene phenol 1-phenethanol 3,5-dimethylpiperidine 1-piperidinocyclohexene biphenyl 1-phenylcyclohexanol 1-pPhenylcyclohexene 1-piperidinocyclohexylcarbonitrile 1-cyclohexylpiperidine Method PCP-GCQ2 Internal Standard Stock Solution: 0.4 mg/ml docosane in chloroform. Standard Solution Preparation: Accurately weigh and prepare a standard solution of phencyclidine (hydrochloride or base) at approximately 0.4 mg/ml using above internal standard stock solution. Sample Preparation: Powder: Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution. If necessary, dilute the sample so the final concentration approximates the standard concentration. Liquid: Accurately pipette an aliquot of the sample into a volumetric flask and dilute to volume with internal standard stock solution. Dilute the sample so the final concentration approximates the standard concentration. Plant material: Accurately weigh an amount of sample into a container and add an accurate volume of internal standard stock solution. Allow the phencyclidine to extract from the plant material for at least two hours. If necessary, dilute the sample so the final concentration approximates the standard concentration. Filter sample prior to injection. Instrument: Column: Carrier gas: Gas chromatograph operated in split mode with FID 5% phenyl/95% methyl silicone 30 m x 0.32 mm x 0.25 µm film thickness Helium 2.0 ml/min Temperatures: Injector: 280 C Detector: 280 C Oven program: 250 C isothermal Injection Parameters: Typical Retention Time: Split Ratio = 60:1, 1 µl injected Phencyclidine: 1.86 min Docosane: 2.39 min
8 Linear Range: Base: mg/ml Hydrochloride: mg/ml Repeatability: Base: RSD less than 0.3% Hydrochloride: RSD less than 1.2% Correlation Coefficient: Base: Hydrochloride: Accuracy: Base: Error less than 5% Hydrochloride: Error less than 5% The following compounds typically found in liquid phencyclidine samples were found to separate with a resolution greater than 1.5: piperidine cyclohexanone bromobenzene phenol 1-phenethanol 3,5-dimethylpiperidine 1-piperidinocyclohexene biphenyl 1-phenylcyclohexanol 1-phenylcyclohexene 1-piperidinocyclohexylcarbonitrile 1-cyclohexylpiperidine Method PCP-GCQ3 Internal Standard Stock Solution: 0.4 mg/ml docosane in chloroform. Standard Solution Preparation: Accurately weigh and prepare a standard solution of phencyclidine (hydrochloride or base) at approximately 0.4 mg/ml using above internal standard stock solution. Sample Preparation: Powder: Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution. If necessary, dilute the sample so the final concentration approximates the standard concentration. Liquid: Accurately pipette an aliquot of the sample into a volumetric flask and dilute to volume with internal standard stock solution. Dilute the sample so the final concentration approximates the standard concentration. Plant material: Accurately weigh an amount of sample into a container and add an accurate volume of internal standard stock solution. Allow the phencyclidine to extract from the plant material for at least two hours. If necessary, dilute the sample so the final concentration approximates the standard concentration. Filter sample prior to injection. Instrument: Column: Gas chromatograph operated in split mode with FID 100% methyl siloxane 12 m x 0.20 mm x 0.33 µm film thickness
9 Carrier gas: Helium 1.0 ml/min Temperatures: Injector: 270 C Detector: 280 C Oven program: 250 C isothermal Injection Parameters: Typical Retention Time: Linear Range: Split Ratio = 40:1, 1 µl injected Phencyclidine: 0.89 min Docosane: 1.29 min Base: mg/ml Hydrochloride: mg/ml Repeatability: Base: RSD less than 0.3% Hydrochloride: RSD less than 1.0% Correlation Coefficient: Base: Hydrochloride: Accuracy: Base: Error less than 5% Hydrochloride: error less than 5% The following compounds typically found in liquid phencyclidine samples were found to separate with a resolution greater than 1.5: piperidine cyclohexanone bromobenzene phenol 1-phenethanol 3,5-dimethylpiperidine 1-piperidinocyclohexene biphenyl 1-phenylcyclohexanol 1-phenylcyclohexene 1-piperidinocyclohexylcarbonitrile 1-cyclohexylpiperidine 5.2. HIGH PERFORMANCE LIQUID CHROMATOGRAPHY Method PCP-LCQ1 Internal Standard Stock Solution: 0.1 mg/ml strychnine in mobile phase. Standard Solution Preparation: Accurately weigh and prepare a standard solution of phencyclidine (hydrochloride or base) at approximately 0.2 mg/ml using internal standard stock solution. Sample Preparation: Powder: Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution. If necessary, dilute the sample so the final concentration approximates the standard concentration.
10 Filter sample with 0.45-micron filter prior to injection. Instrument: Column: Detector: Flow: High performance liquid chromatograph equipped with diode array 5µm ODS, 150 mm x 4.6 mm UV, 210 nm 1.5 ml/min Injection Volume: 5.0 µl Buffer: 4000 ml distilled water, 10 g sodium hydroxide, 30.0 ml phosphoric acid and 8.0 ml hexylamine Mobile Phase: Buffer: acetonitrile 80:20 Typical Retention Time: Linear Range: Phencyclidine: 4.42 min Strychnine: 1.70 min mg/ml Repeatability: RSD less than 2% Correlation Coefficient: Accuracy: Error less than 5% The following compounds typically found in liquid phencyclidine samples were found to separate with a resolution greater than 1.5: piperidine cyclohexanone bromobenzene phenol 1-phenethanol 3,5-dimethylpiperidine 1-piperidinocyclohexene biphenyl 1-phenylcyclohexanol 1-phenylcyclohexene 1-piperidinocyclohexylcarbonitrile 1-cyclohexylpiperidine 6. QUALITATIVE DATA 6.1. ULTRAVIOLET SPECTROPHOTOMETRY SOLVENT MAXIMUM ABSORBANCE (NM)
11 Aqueous Acid 258 See spectra on the following pages for FT-IR, FT-Raman, Mass Spectrometry, Nuclear Magnetic Resonance, and Vapor Phase IR. 7. REFERENCES Budavari, S., The Merck Index, 12 th Edition, Merck and Co., Inc., 1996, p Clark C.C., Journal of Association of Official Analytical Chemists, Vol. 62, 1979, pp Clarke, E.G.C., Isolation and Identification of Drugs, 2nd Edition, The Pharmaceutical Press, Cone E.J., Darwin W.D., Yousefnejad, D. and Buchwald, W.F., Journal of Chromatography, Vol.177, 1979, pp Henderson and Davis, "The Identification of Phencyclidine in Clandestine Laboratory Liquids", Microgram, Vol. XXIV, No. 11, November 1991, pp Kalir A., Edery H., Pelah Z., Balderman D. and Porath G., Journal of Medicinal Chemistry, Vol. 12, 1969, pp Maddox V., Godefroi E. and Parcell R., Journal of Medicinal Chemistry, Vol. 8, 1965, pp Personal Communication, Norman Mausolf Peterson R. and Stillman R., Phencyclidine (PCP) Abuse: An Appraisal. Department of Health, Education and Welfare, Raney J., Skowronski G. and Wagenhofer R., Microgram, Vol. XIV, 1981, pp ADDITIONAL RESOURCES Forendex Wikipedia
12 FTIR: Phencyclidine Base in KBr 16 scans, 4 cm -1 resolution %T Wavenumbers (cm-1) FTIR: Phencyclidine hydrochloride in KBr 16 Scans, 4 cm -1 resolution %T Wavenumbers (cm-1)
13 FTIR (ATR): Phencyclidine 16 scans; 4 nm resolution DTGS KBr Detector, Avatar System %T 70 PHENCYCLIDINE HCl (ATR) Wavenumbers (cm-1) %T PHENCYCLIDINE BASE (ATR) Wavenumbers (cm-1)
14 RAMAN: Phencyclidine 256 scans; 4.0 nm resolution, InGaAs detector, Nicolet 6700 PHENCYCLIDINE BASE In t Raman shift (cm-1) PHENCYCLIDINE HCl Int Raman shift (cm-1)
15 MS: Phencyclidine as103phencyclidine # RT: AV: 5 SB: , NL: 5.34E6 T: + c Full ms [ ] m/z MS (ESI): Phencyclidine in MeOH; Electrospray ionization; Full-scan positive ion mode; quadrupole ion-trap analyzer. Phencyclidine_MSMS #25-50 RT: AV: 13 SB: , NL: 3.94E7 T: + c ESI Full ms [ ] m/z Full scan: molecular weight information (M+H+)+
16 MS/MS: Phencyclidine in MeOH; Electrospray ionization; MS/MS positive ion mode; quadrupole ion-trap analyzer. Phencyclidine_MSMS #23 RT: 0.29 AV: 1 NL: 8.28E5 F: + c ESI d Full ms @35.00 [ ] m/z Tandem MS: MS/MS using standard collision energy of 35 ev.
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19 Normalized Intensity Normalized Intensity Normalized Intensity No. (ppm) Height FT-NMR 400 MHz Proton Phencyclidine HCl in D2O (60 mg/ml) No. (ppm) Height Chemical Shift (ppm) Chemical Shift (ppm) Chemical Shift (ppm)
20 Normalized Intensity FT-NMR 400 MHz Carbon Phencyclidine HCl in D2O (60 mg/ml) No. (ppm) Height Chemical Shift (ppm)
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